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Named for the Japanese word for enlightenment, this boutique property marries classic Cycladic architecture (cube-shaped structures, whitewashed stone walls, arched entryways) with the clean lines of locally made furnishings in naked wood. None of the 25 rooms and 10 suites are the same, but most have private outdoor whirlpools or plunge pools, plus plush beds that make it impossible to leave. Nearly all of the public spaces, however, offer stunning views over Mykonos (about 1.5 miles away) and the bay, and make striking use of night-lighting, especially at the pool, which is built into the natural rock face. A grottolike spa features two treatment rooms, a futuristic-looking whirlpool area, and a hammam for stylish pampering sessions. The hotel offers complimentary transportation to Mykonos, but with its inviting Bar & Sunset Lounge and a restaurant that is garnering awards and accolades, you may decide to stay put for the duration of your vacation.

While the Cycladic island of Serifos has stayed blissfully under the radar for most tourists, savvy Athenians have been quietly snapping up property while preserving its dusty charms. COCO-MAT Eco Residences, opened by the eponymously named Greek sleep-product company, is emblematic of this mindset: Its 13 rooms were reclaimed from stone miners’ houses built in 1910 at the foot of a hillside, just steps from the sand and calm waters of Vagia Bay. The one- or two-bedroom units feature bedrooms on the (cooler) bottom floor and living spaces and kitchenettes above (they’ll do the grocery shopping); you choose your mattress preference from the brand’s sustainably made line. Carved into the cliff face, the Lounge Bar serves buffet breakfast in the morning, lunch and light snacks during the day, and dinner in the evening—including right on the shore (for an additional charge). The hotel also supplies car or motorcycle rentals should you want to explore the island, and also will arrange diving trips and excursions to different beaches.

You can’t beat this - a delicious, freshly caught seafood dinner on the edge of the Aegean Sea. Sunset Taverna is located in Ammoudi, at the base of the cliffs in Oia, Santorini - dramatic scenery for simple, rustic, delicious food. From the castle in Oia, enjoy a leisurely, winding walk down to the marina (or take a car down the coastal road). Feast on lobster spaghetti, fresh grilled seafood, baked feta, stuffed eggplant, Fisherman’s Salad. Hike back up to Oia under the clear, starry night.

If you dream of a tranquil island free from traffic and the din of human activity, where donkeys are the only means of transportation, Hydra is it. Beautiful Mediterranean waters, cobbled streets, and preserved architecture makes Hydra an idyllic getaway. Spend a day here, and you’ll know why famous artists like Leonard Cohen made this place their second home. There’s even a fan festival dedicated to Cohen here once a year.

There are dozens of archaeological museums in Greece, but this is easily the biggest and best. Over 11,000 exhibits—including golden death masks, larger-than-life bronze gods and black-and-terracotta pottery—provide a panorama of Greek civilization from prehistory to late antiquity. Standouts are the Antikythera Mechanism, the world’s first analog computer, which lay under the sea for 2000 years, and enchanting wall paintings of boxers and blue monkeys from Santorini, buried under volcanic ash around 1600 B.C.E. Although the curation is somewhat old-fashioned, the collection is truly one-of-a-kind and requires several hours (if not several days) to explore. Afterwards, have an iced coffee among the ethereal statues in the walled garden.

This little private church is probably the most photographed stop in Oia. Our rented house was right next to it but lower on the steps so we could see lots of people getting lots of photos. Married couples would take their photos next to it, photographers were offering workshops that included this spot. I woke up at 5.30AM to wonder when nobody else was around. Best time of day to walk around this very busy tourist destination.

A neoclassical building in Plaka thoughtfully renovated into a boutique hotel, the ZIllers has ten guest rooms and a rooftop restaurant and bar. The building was designed by Ernst Ziller, a German architect whose work can be seen all around Greece, notably at Athens’ National Theatre, Presidential Mansion, and the Goulandris Museum of Cycladic Art. The original high ceilings, wood floors, and wrought iron-balconies have been retained and refreshed with a modern minimalist decor. While value priced, rooms with atrium views can be dark and Acropolis views are worth the upgrade. Rates include breakfast served in room or on the rooftop, book ahead for dining at other times as it is popular with locals. The contemporary Greek menu might include shrimp with buffalo milk couscous or sea bass in a dill and lime foam, plus innovative desserts like Greek coffee mousse with olive oil jelly. Location is also faultless, overlooking the Athens Cathedral, and a five-minute walk from Monastiraki or Syntagma Square.

Amorgos is one of the few Cycladic islands where kafenio culture continues to thrive. Every village has at least one kafenio, the traditional café-cum-grocery-cum–community center, where old-timers play cards or argue about politics over ouzo mezes. O Prekas, on the waterfront of the port of Katapola, even serves as a travel agent. The decor has barely changed since it was founded in 1950, with its patterned floor tiles, neat rows of tin retsina jugs, black-and-white photographs, and a collection of vintage radios. It’s the perfect spot to share heaped plates of crunchy whitebait and grilled octopus as you watch the fishermen and ferry boats come and go.

While most visitors to Santorini squeeze along the cliffs of Oia to watch the sunset, those in the know kick back on the vine-shaded terrace of the Sigalas winery with a bottle of crisp assyrtiko and a platter of Cycladic cheeses and cherry tomato chutney. Winery tours include the opportunity to try 10 of Sigalas’s superb wines alongside an array of excellent mezes. For a special treat, book ahead for the six-course tasting menu paired with Sigalas’s finest vintages. Delicate but intensely flavored dishes—cucumber gazpacho, white eggplant layered with goat cheese and pine nuts, sea bass carpaccio with beet jus and citrus mousse—taste even better as dusk bathes the plain of Baxedes in a golden glow.

Once you’ve seen the Blue Monkey fresco and other masterpieces in the Museum of Prehistoric Thera, you may want to take some of the delicate and timeless art of Minoan Santorini home with you. Replica in Oia specializes in exactly what its name implies—museum-quality replicas. Some of our favorite items are the white Cycladic idols that are particularly beautiful and still look surprisingly contemporary after all these centuries.

The ancient Greeks called Folegandros “iron hard,” but this Cycladic island has a mellow soul beneath its edges. The northern part is the wildest, where locals still scrabble a living making cheese from their goats, threshing grain with mules, and fishing off translucent bays. At homestead tavernas (like Eirini’s grocery-cum-eatery in Ano Meria), the owners rear or grow everything they serve. The main village, Chora, is huddled on a cliff 650 feet above the sea, but the emerald water below is so clear you can count the fish swimming by. The tangle of lanes all lead to three interlocked squares lined with tavernas and bite-size bars, where evenings drift by as you drink shots of rakomelo (warm grappa with honey).

Part of the Cyclades, this Mediterranean retreat is complete with white beaches and crystal blue waters, pottery making that dates back thousands of years, and villages that uphold ancient traditions. But what really makes this island stand out from the rest is a historic culinary scene that continues to thrive. Sifnos is the birthplace of the first Greek cookbook, written in 1910 by chef Nicholas Tselementes. Over the years, celebrity Greek chefs have opened up restaurants next to local eateries whipping up traditional dishes, from mastélo (goat or lamb cooked in red wine) to chickpea balls flavored with herbs.

A few kilometers inland from Mykonos Town, Ano Mera is a small Cycladic idyll of a village. To get a feel for how people lived before the tourism boom, wander the streets and smell the scent of fresh baked bread. The Panagia Tourliani church and the Paleokastro Monastery are centuries old, and you can also find graves of the ancient Geometric era of Greece here.

More and more cruise ships are arriving to the well-known Greek islands for day exploration. And while that is a boon to the local economies; crowded restaurants and beaches are not what you have come to experience. Some of these popular islands actually have very few year-round residents as the cruise visits are seasonal. So that “real Greek” town that you came to see, really isn’t. The solution? Try one of the lesser-know but equally beautiful Greek Islands like Ios in the Cyclades Islands. Here you’ll find five-star hotels, mom and pop inns, historical monuments, miles of sparkling beaches, dynamite restaurants, vibrant mountain towns, incredibly reasonable shopping, breathtaking vistas, and local wines, but most of all Ios can be your own paradise. The island of Ios is still a place where real people live and work, but there is plenty of support for tourism (sometimes it’s party central at Mylopotas Beach) and you will find true hospitality, safe streets to wander and new activities like the recently opened hiking path system. Imagine walking at your own pace to archeological sites, beaches, churches and mountain villages just like the early inhabitants did for centuries? The Greek Cultural Mountaineering Club of Fyli has long wanted to repair and connect the ancient paths and a few months ago the project was completed with the help of volunteers and the Municipality of Ios. Over thirteen kilometers of paths are open and well-marked by signs connecting other paths and old roads of Ios for you to enjoy. Not a hiker? The shopping is sublime. Not for the collectors of designer handbags but those desiring handmade leather sandals, precious gem jewelry and smart local-style clothing designs. Lounging by the pool is always a favorite. Stay at the elegant Liostasi Suites and you will be pampered like a jet-setter. Wish for a low-key stay? The Pavezzo Hotel and Suites is painted in beautiful colors and embellished by flowers offering family-style rooms, rooms for one or two and vantage points with sea views set on the side of a mountain with cooling breezes and the friendliest owners. If you are a fan of Greek cuisine there are many terrific restaurants, some right on the ocean like Drakos Taverna at the end of Mylopotas Beach. A favorite in Chora, the town above the Ormos harbor which is completely accessible on foot, is Elia. Visit the cathedral and one of old windmills the island is famous for while wandering the maze of winding stone streets that spill down from top of the hill. Or down in Yialos by the harbor pop into one of the very casual tavernas. Be sure to visit the food shop called Mosenta at the port to watch them create, and for a taste of sesame seed and honey cakes. They also package local wild herbs and make a great body cream that is made from their own honey and olive oils. Insider Tips: Go in Fall for peace and quiet and best rates on rooms. There is no airport so take the ferry from Pireaus, Athens or Santorini. Images Kurt Winner Photography

My island destination has to have very few things to make me happy, but I always insist on them. And if they don’t have then, well that’s a deal breaker. Milos, part of the Island chain of Cyclades has them all. I want a clean room with a comfy bed, overlooking the ocean- check. I’d like a cool drink on a hot afternoon in the village taverna or while enjoying a swim at the beach- yes they have it. I want to sit by the sea and enjoy the sunset turn brilliant shades of orange and gold-yupppers. But Milos has so much more. The Aphrodite of Milos or the Venus de Milo was found here in the 1800’s by a wandering islander. The French soon ran off with the beautiful Greek woman from 100- 130 BC and put her in the Louvre so all could adore her, although she probably preferred the Greek island life, because she was dressed for it. The Franks stopped by and built a castle ostensibly to protect their interests in the Mediterranean. A plethora of hot springs to bathe in dot the island and there is fresh seafood and wine, and stunningly captivating white villages sparking in the sun. This island of Milos is a pearl, and worth a stay during your Greek island tour. How to arrive? Take the various ferries or charter a sailboat or yacht. http://www.milos.gr/en/